The War for Late Night

by Carter, Bill

  Throughout the quick demise of his MTV and syndicated shows, his passage in and out of dalliance with the movies, and his unrequited affair with David Letterman’s production company, Stewart built his reputation with consistently impressive work. Everybody who worked with Jon came away thinking they had just encountered a driven, creative, and, yes, appropriately neurotic future star. All it would take was the right launch module.

  The Daily Show was precisely the rocket he required. Stewart’s sensibility—and his insight that the show’s comedy should have a harder edge about the folly of both those in the news and the people in the media who were covering them—transformed TDS first to more smart than silly, and then from awfully smart to damn brilliant. By 2000 it was celebrated enough to start grabbing Emmy nominations and ultimately collecting awards.

  At the prime-time Emmy Awards ceremony in Los Angeles on September 19, 2004, Conan O’Brien sat with his group in the audience, close by Lorne Michaels, who, since he still retained an executive producer credit on Late Night, would take home a prize if Conan’s show won for best comedy or variety show. Michaels was also present because his meal ticket, Saturday Night Live, had been nominated in the same category.

  Almost every season both shows would share the nominations with Letterman, perhaps Bill Maher’s HBO series, and inevitably with The Daily Show. Inside Conan’s camp the frustration mounted: starting in 2003 Jon Stewart’s show racked up wins every year in that category as well as the best-writing award, a streak that would continue right through 2009. As much as Conan and his group tried to shrug off Stewart’s success—topical and political humor always impressed awards types, they reasoned—it quietly drove them all nuts. They had all worked so hard, come up with so much distinctively original material, but they never got a shot to be recognized—because Jon Stewart was always there.

  Michaels, who was losing every year as well with SNL, was more philosophical about Stewart’s winning streak. With his insight into Conan’s darker side, he knew this level of frustration with Stewart’s Emmy dominance could not be productive for the melancholic Irish comic. So, just as the telecast began, Lorne thought he should offer a helpful observation.

  “Look around this room,” he said to Conan. “Do you see anyone who looks like you in this room? You know, there are a lot of very small Jews in the room.”

  Lorne himself fit that description, though perhaps not as precisely as Stewart. But the joke was meant to let Conan know both that he shouldn’t take the Emmy voting too seriously and that Jon Stewart was no fluke. He was going to be around as a formidable player in late night.

  Leno had a similar impression, which was why he feared a double-pronged assault from OʹBrien and Stewart. Leno refused to acknowledge any Emmy envy, however. He was never nominated anymore, which he put down to a typically perverse Hollywood dismissal of the merely popular. Jay would take numbers over trophies anytime. He had made that bargain with himself long before.

  When Jay Leno was the most frequent—and popular—guest on David Letterman’s Late Night show in the 1980s, he eagerly embraced the role he had then carved out for himself: Mr. Cutting-Edge Comic. Letterman fans loved him for his ferociously funny harangues on the absurdities of life. Dave would simply set him up with “So what’s bothering you this time, Jay?” and Leno would be off, ranting about this idiocy (airline flights, bad movies) or that (corporate greed).

  It gave him a profile in the business, which is what he wanted. But it wasn’t all he wanted. That level of success might make him money and attract favorable critical notices, but Jay was after the ultimate comedy career, and the models there were not Letterman or Richard Pryor or Sam Kinison. Jay consciously set out to have the career that a Bill Cosby or a Johnny Carson or—even more aptly—a Bob Hope had had. He wanted to be a comic for every audience.

  That meant jettisoning Mr. Cutting Edge and slipping into Mr. Regular Guy. That persona was a snugger fit for Leno, anyway. He often joked about being “a great believer in low self-esteem,” but he came by the quality honestly.

  One constant figure played a central role in Jay’s act, and in most of his stories about the formation of his character and views on life: his mom. Mainly Jay made merry references to his mother’s habitual embarrassment and emotional stringency, qualities he summoned up when discussing why he never wanted the title of his show to be the “Tonight Show Starring Jay Leno” as it had been with Carson, but instead insisted on the “Tonight Show with Jay Leno.” “Why would you want to call attention to yourself like that?” Jay would say, imitating his mother’s pinched Scottish accent. Of course, while the disavowal of “starring” also played well with that everyman image he sought to cultivate, the frequent citation of his mother’s cringing discomfort with his fame came from a deeper place.

  James Douglas Muir Leno grew up in Andover, Massachusetts, feeling like a townie in a village dominated by its illustrious prep school, Phillips Academy. His exposure to that elite world gave Leno insight into what he concluded was the fundamental prep school mentality: class superiority. Jay himself was a child totally outside the WASP culture. His father, Angelo, son of Italian immigrants, was a popular insurance salesman for Prudential, and the family took pride—“That’s our company!”—when those “piece of the rock” commercials would play on television during shows of the fifties like Victory at Sea. His mother, Cathryn Muir, had survived a difficult childhood. She was sent to America from Scotland at age eleven to live with an older sister, because her mother had abandoned the family for a younger man and her father couldn’t afford to take care of all his children at home. Her formal education never extended past second grade. As Jay saw it, the experience had left her with an air of sadness that permeated her life.

  Jay was born when Cathryn was forty-one, and his only sibling—a brother, Patrick—was ten years older. Jay acknowledged that he had never been close to Patrick, which had in part to do with their age difference, but also with the fact that Patrick was remarkably gifted academically. He was one of the top students in New England in high school and won an ROTC scholarship to Yale. After graduation he became an army officer, serving in Vietnam, and then it was on to law school. For a woman who never had a chance to get beyond second grade in elementary school, this outstanding, high-achieving son was naturally a source of huge pride.

  At the same time that she basked in the glory of Patrick’s intellectual accomplishments, Cathryn Leno found herself often trudging off to school in Andover to hear about the latest embarrassing tribulation her younger son had brought upon the family. Teachers discussed Jay’s lack of attention and his apparent interest only in cutting up and amusing his classmates. The highlight of this experience, as Jay wove the tale (and fair context demands a note that Jay can be a world-class fabulist in the service of a humorous story), took place with a guidance counselor in high school, Mr. Neal, who decided that Cathryn had to be brought in for a conference. Jay always claimed he “overheard” the subsequent conversation: “Mrs. Leno, have you thought of taking Jamie out of school? He works at McDonald’s now and he seems to like that. Maybe he would do better at something like that. You know, education’s not for everyone, Mrs. Leno.”

  As Jay remembered it, his mother was furious, telling Mr. Neal she had never heard of a guidance counselor suggesting a child be taken out of school. “Well, he’s disruptive,” the counselor complained. And then his mother took a stand, saying she was not doing anything of the sort and Jamie would stay in school to get his high school diploma.

  Whether actually diagnosed or not, Jay made reference to his school difficulties by explaining, “I’m a little dyslexic.” His mother’s reaction to this was what Jay came to call her mantra: “You know you’re going to have to work a lot harder than the other kids to get the same things they have.” Leno seared that advice into his psyche. If he wasn’t as gifted as other kids—later, other comics—he would hit them where they might be weak: their work ethic. Leno especially loved to tell one story ab
out his early days as Tonight Show host. He was at his post at home, as usual, writing jokes for the next day’s monologue, when he turned on the TV and saw a competitor. (Jay didn’t mention the name because he had resolved his differences with the rival, and good relations carried enormous weight with Jay, but it was pretty obviously Arsenio Hall.) “There he was sitting at the Lakers game,” Jay recalled. “And I thought, ‘Got ya! I’ll have a monologue tomorrow night and you won’t.’ And you know what? He didn’t.”

  For Jay, the job always seemed to be as much about the self-abnegation involved in the effort as the effort itself: “It just seems like common sense. If you go to a party, or go out drinking, I win. It doesn’t seem that hard to understand. I’m amazed at people who can’t get that.” (Jay swore that he had never consumed an alcoholic beverage in his life. Of course he never took drugs, either, and, he said, he steered clear of caffeine as well.) How much of this attitude was a function of his relationship with his mother was always difficult to guess for those close to Jay, because Leno rarely exposed his emotions. But Jay brought his mom up often, on stage and off, and usually in the context of how repressed she was.

  Like in his story about Carnegie Hall. As his career was taking off, thanks to his many breakthrough appearances on Letterman (sixty, he estimated at this point), Jay was booked in the hallowed New York concert venue. At first, he said, his mother found this simply astonishing. “Why are you going to be in Carnegie Hall?” he quoted her. “She thought it was a mistake.”

  But of course he wanted his parents at such a prestigious show, and he got them excellent tickets in the third row back, right in the center. Behind them was a row of seven or eight college-age guys. “These guys knew all the bits from watching Letterman,” Jay said. “So whenever I started something they recognized, these guys would go woo, woo and start to laugh and applaud.” Jay threw himself as usual into the bit but could not help noticing from the stage that his mother was turning around in her seat.

  “She starts to go, ‘Shush! Shush!’ She’s trying to shush them.”

  Appalled, Jay stopped his act to speak out to his mother. “Mom! You don’t shush people.” He realized it was another example of his mother being somehow humiliated and embarrassed by the attention he was getting. It made her completely uncomfortable.

  Her discomfort seemed amplified when the contrast between her sons grew wider. Patrick’s life took unexpected turns, all unhappy in various ways—his marriage, his career. Jay, meanwhile, thrived. He started making solid money as a comic at a remarkably young age and was able to buy a house before all the other young comics in the LA scene at the time. He got on television. He was, of all things, booked into Carnegie Hall.

  And then, The Tonight Show beckoned. It should have been a glorious accomplishment to share with his family, but it didn’t quite go that way. Jay sensed that Patrick had issues accepting his kid brother’s success. And his mother seemed to resist expressing a lot of joy about it as well. Jay, making millions, could afford to give his parents anything, but that became a sensitive area. Sometimes Jay would return home to Andover with an expensive gift for his mother—a piece of costly jewelry, for example. Jay would present it to his mother, who would quickly get fluttery and say, “Don’t tell your brother you bought this,” and then would run and hide the gift away.

  Jay would explain all this and say he understood it; his brother had to feel cheated in certain ways. Patrick was stuck with the Scottish traits in the family; Jay inherited the Italian. (That’s where the good teeth and fantastic head of hair came from.) Patrick became a worrier, stressed over everything in his life. It only swelled the cloud of sadness that hung over his mother.

  Jay’s confidants—and they were few—could only draw inferences from the snippets of his background that he dropped here and there. Jay never spoke of his mother without evident deep affection. Still, if some suspected that Jay had missed out on a full, externally expressed measure of motherly love, leaving him with a hole in his heart that he could never fill, and even refused to address, he was certainly no candidate for therapy. Jay disdained any kind of psychological mumbo jumbo, and not just because as a comic he was supposed to make fun of people’s foibles. Leno was not inner directed because he was primarily joke directed. He stripped away almost any other interest—other than his vehicles, which he worked on avidly, filling just about every waking hour when he wasn’t writing or telling jokes. He certainly didn’t chase women. His marriage to Mavis did not strike colleagues as gooily romantic (they didn’t seem to spend much time together), but it was, by every indication, solid and comfortable to both. Jay, in establishing his mainstream bona fides, would always point out, “I’m still on my first wife.”

  He and Mavis had never had children. They rarely vacationed together, mainly because Jay abhorred the very idea of vacation. During weeks off he booked himself into Vegas or some high-paying corporate retreat, while Mavis often traveled the world. Jay loved to tell a story of an ill-advised decision to take a booking in Hawaii, with an extra day scheduled afterward to relax on the beach. A morning on the beach led him to wonder if his watch had become filled with sand, because it indicated that only an hour had gone by when surely he had been out there all day. He was on a plane back to LA before noon. Jay also famously asked NBC to consider hiring a separate staff of writers and producers for the six-to-eight-week period that the show was scheduled to be dark so he could work all fifty-two weeks of the year while the rest of the regular staff got a break. (NBC politely declined.)

  His aversion to going anywhere except places where he could tell jokes led to his making pronouncements that even his closest associates acknowledged sounded bizarre. “You start taking vacations and you go, ‘Uh-oh, what if I like this?’ Then you’re screwed.” The whole notion of going somewhere and doing something simply because it was pleasurable or interesting was a concept Jay simply didn’t get. “I understand how people spend money to buy things they need or they like,” Jay said, summarizing his philosophy. “But spending money on an experience? That seems like an extravagance to me.”

  Of course, even though he always avowed that he never spent a dime of his NBC salary and lived only off the money from his stand-up dates, it didn’t seem to dawn on Jay that most of the people coming to see him tell jokes were on vacation and were paying for that experience.

  Critics—as well as occasionally the network and his own producers—often cited Jay’s apparent lack of interest in the stories guests on the show told. Certainly most of the staff knew that Jay devoted little time preparing to speak to guests. Worse, at least for some, was a habit Jay adopted later in his Tonight Show run. As described by one A-level movie star guest, an appearance with Jay could be thoroughly disconcerting.

  “I’m sitting there telling him a story about some damn thing that happened and I realize he’s not looking at me at all,” the star said. “His eyes are going straight past me. The audience can’t see this because he’s still looking vaguely in my direction, but his eyes are not on me at all. When he went to commercial I took a look over my shoulder. There was a guy with cue cards standing off to the side behind him. Jay was just reading the questions off the cards. Not paying attention to me at all. The whole thing was so artificial; I was totally put off by it.”

  Jay’s day was so consumed with reading and deciding on jokes that he usually had to be clued in that it was time to stop. “By the afternoon he would have been reading jokes for about five hours,” one longtime staff member said. “He would have culled them down to about a hundred fifty by that point from at least five hundred. Then about four p.m. someone would go to him and say, ‘You can’t read any more jokes.’ He would go down to rehearsal, but while rehearsing whatever the comedy bit was in act two, Jay would still be reading more jokes right through the rehearsal.” Throughout the process, Jay would rarely, if ever, laugh.

  But for Jay his method worked. Forget the Emmy Awards, the critics, the comparisons to Dave or anybody else
. Others might watch him and shake their heads in wonder. Some might call him a robot, with no apparent inner life at all. Jay didn’t care, nor did he even seem to disagree all that much. He had boiled it all down to the most basic level, in a way that made others in the field of comedy sometimes wince and moan. No matter; Jay stuck steadfastly to his approach. After all, it was the secret to his success:

  “Write joke; tell joke; get check.”

  CHAPTER FIVE

  SEIZE THE JAY

  For six months or so Jay Leno would be fine.

  Throughout the fall of 2004 and early 2005 his routine would be as it always had been. Around first light he would climb into his chosen vehicle for the day (1937 Bugatti, 1955 Buick Roadmaster, 1915 Hispano-Suiza, 1987 Lamborghini Countach, 1934 Rolls, 1996 Dodge Viper, 1926 Bentley, 1932 Duesenberg, 1909 Stanley Steamer—whatever choice from his ever expanding collection he and his garagemates had most recently restored to full driving condition) and make his way over the hill to Burbank from his home in Beverly Hills. Upon arriving on the NBC lot he would park in his designated spot adjacent to the entry ramp, pull out his battered leather saddlebag of a briefcase stuffed with jokes and the research the staff had provided on news stories and guests, and roll on in to work.

  Many mornings the first one in, he’d settle down at his desk and pore over the jokes he and his head writer Joe Medeiros had committed to index cards late the night before in Jay’s home office. At the same time he would be culling printouts of the e-mailed jokes that had been submitted by the group still known as the faxers (a holdover from a bygone technological day), the pay-by-the-joke freelance contributors who got seventy-five or a hundred dollars apiece for every gag Jay used on the air.